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If web gaming is legalized, the self-made multibillionaire and mega-donor insists, big-name Silicon Valley companies will invest heavily in the business, eventually coming to dominate the market with their superior technology and global reach. States will smell money and levy taxes. And then it will happen: the apocalypse, sayeth the Cassandra of gaming soothsayers, who is putting his fortune where his crystal ball is.

“Somebody like Google or Facebook, they’ve got a billion customers hitting them every day,” marveled Adelson, who chairs Las Vegas Sands, which owns the Venetian and the Palazzo on the Las Vegas Strip, in a lengthy recent interview. “They’ll come in there, they’ll squash the other guys like … you squash the little ant running across the table or the floor and that’s going to be the end of all of it.”

Is this man bluffing?

“I’ve been an entrepreneur for 68 years,” the 80-year-old casino mogul told me as we sat in a conference room at his offices at the Venetian, a cavernous space with one entire wall festooned with magazine covers with his picture. He was surrounded the entire 75 minutes during this rare sitdown by two aides and his wife, Miriam, a success in her own right as a doctor who specializes in addiction. “I’ve never failed yet. And I’m telling you, the one characteristic of a successful entrepreneur is to have courage and belief in your own convictions.”

If there’s one thing Adelson believes in, it is himself. The octogenarian who parlayed a computer trade show into a billion dollars, sold it in 1995 and bought the place where the Rat Pack hung out, then erected the Venetian where the Sands once stood, knows not of equivocation. And if you listen to him talk about the dangers of web gaming, he does not vacillate, he does not doubt, he does not flinch.

Adelson has said he will spend whatever it takes— he is worth an estimated $37 billion and his earnings dwarf those of all other gaming companies—embarking last fall on what a rival calls a “jihad” to stop Internet wagering and threatening to use his ample political muscle as the country’s largest GOP donor to stop what many think is unstoppable. Now, he’s funded an anti-web gaming coalition, tapped former politicians as mouthpieces and vowed to go state by state to end the scourge.

He cannot be ignored. But despite his undeniable successes in the convention business and in the hard-knocks world of casinos, Adelson has mostly failed at the one business he needs to excel in to achieve his goals now: politics. From seeking to control local elected boards and defang unions to bankrolling pro-Israel groups opposed to Middle East peace talks to spending at least $100 million in 2012 to oust President Barack Obama, Adelson has given much and reaped little.

There are, of course, 37 billion reasons why Sheldon Adelson is still a force to be reckoned with. But this is a fight he just might not win.

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Adelson stayed ahead of his rivals by building gambling outposts overseas, like the Macao casino shown here. | AP Photo

Adelson’s unlikely foe is the American Gaming Association, the industry’s main lobbying shop, most of whose members—save Adelson—favor online gaming. After Adelson launched his Coalition to Stop Internet Gambling last month, the AGA mounted a counteroffensive, building its own coalition and hiring the likes of Obama guru Jim Messina.

Adelson has pushed back—hard. He derides his rival Caesars Entertainment, which is leading the AGA’s online gaming push, as a debt-ridden, dead company trying to reanimate itself via the web and thereby threatening the future of the entire industry. “They’re completely broke,” Adelson said of Caesars, which stands $24 billion in debt. “You know, the old expression, ‘If you’re so smart, why ain’t you rich? If they’re so smart, why aren’t they successful? I’ll tell you the truth: I don’t think they know what they’re doing.”

This is Subtle Sheldon at work, leveling a broadside at the second-largest gaming company in the world and specifically at Caesars CEO Gary Loveman, a wonkish, 53-year-old MIT Ph.D. who once taught at Harvard University. Many who watch the growing war over gambling’s online future see the whole thing as mostly an Adelson vs. Loveman affair—and it is getting nasty.

“Since [Adelson] is an avowed non-computer user, an Internet virgin so far as I can tell, he does not know what he is talking about,” Loveman told me. Loveman lieutenant Jan Jones Blackhurst, a former Las Vegas mayor, seems even more upset with Adelson, accusing him of “pandering to fear rather than using facts.”

“Sheldon is not a stupid man,” she said. “He’s just stupid on this issue.”

The history of Nevada’s casino industry is one featuring titanic egos who often disagree but who generally have united in being Chicken Littles about emerging markets. First it was New Jersey in the late 1970s, then tribal resorts, then other domestic jurisdictions, then the Far East. But in every one of those cases, those who were crying wolf soon became the wolves, salivating over the money to be made in the new places and eagerly extending their tentacles to far-flung entrepôts like Singapore and Macau.

Jon Ralston, contributing editor at Politico Magazine, has covered Nevada politics for more than a quarter-century. He has worked for both major Las Vegas newspapers and now has his own site, email newsletter and television program.